dichloro(N-2,2,2-trichloroethoxycarbonyl-2-aminoethyl)phosphate | 32159-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dichloro(N-2,2,2-trichloroethoxycarbonyl-2-aminoethyl)phosphate
• 英文别名: dichloro-<-2-amino>ethyl>phosphinic acid；2-(N-β,β,β-trichloroethoxycarbonylamino)ethyl dichlorophosphate；2,2,2-trichloroethyl N-(2-dichlorophosphoryloxyethyl)carbamate
• CAS: 32159-15-2
• 化学式: C₅H₇Cl₅NO₄P
• 分子量: 353.354
• InChiKey: DKTMLIRQLOBOOL-UHFFFAOYSA-N

物化性质

• 沸点：
  424.4±45.0 °C(Predicted)
• 密度：
  1.675±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  油醇 、 dichloro(N-2,2,2-trichloroethoxycarbonyl-2-aminoethyl)phosphate 生成 Oleyl-phosphoryl-ethanolamin
  参考文献：
  名称：

  抑制肾素活性的溶血磷脂酰乙醇胺类似物的合成。

  摘要：

  通过各自的脂肪醇的磷酸化和膦酰化反应，合成了一系列含有饱和的和亚甲基间断的顺式-烯烃脂肪链的溶血磷脂酰乙醇胺类似物。发现花生四烯酸基和亚麻基磷酰基乙醇胺（12、13），花生四烯酸基（2-邻苯二甲酰亚胺基乙基）膦酸酯（17）和花生四烯酸基（2-氨基乙基）膦酸酯（18）是体外肾素-肾素底物反应的有效抑制剂。较小的不饱和度的溶血磷脂酰乙醇胺类似物14-16是弱活性的或无活性的。在一项初步研究中，向高血压大鼠肌内注射25 mg / kg / day的花生四烯酸（2-氨基乙基）膦酸酯（18）可使血压在3天内显着降低（50 mm）；连续服用18天（15毫克/千克/天）再服用4天后，发现血浆肾素活性为16 ng / 0.1 ml / 15 hr，而最初给药前为69 ng / 0.1 ml / 15 hr。发现花生四烯酸（3），花生四烯醇（8）和几种相应的不是磷酸酯或膦酸酯的四烯酸酯，酰胺，甲磺酸酯和甘油

  DOI：

  10.1021/jm00246a003
• 作为产物：
  描述：

  2,2,2-三氯乙基N-(2-羟乙基)氨基甲酸酯 在 三氯氧磷 作用下， 以 苯 为溶剂， 生成 dichloro(N-2,2,2-trichloroethoxycarbonyl-2-aminoethyl)phosphate
  参考文献：
  名称：

  Chemical synthesis of a polymerizable bis-substituted phosphoethanolamine

  摘要：

  The first chemical synthesis of a 1,2-bis-substituted polymerizable-sn-glycerol-3-phosphoethanolamine is reported. The synthetic approach utilizes the preparation of 1,2-bis(16-methyl-2,4-(E,E)-octadecadienoyl)-3-(4-methoxybenzyl)sn-glycerol via the acylation of 3-(4-methoxybenzyl)-sn-glycerol with 16-methyl-2,4-(E,E)-octadecadienoic acid. The deprotection of the 4-methoxybenzyl ether group is accomplished in high yield via Lewis acid catalyzed hydrolysis at -78 degrees C. The final step is the phosphorylation of this 1,2-bis(dienoyl)-sn-glycerol.

  DOI：

  10.1016/0040-4039(95)01930-g

文献信息

• .omega.-(N-acylamino)alkylphosphoryl ethanolamines, pharmaceutical
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US03985875A1

  公开（公告）日：1976-10-12

  New .omega.-(N-acylamino)alkylphosphoryl ethanolamines and their pharmaceutically acceptable acid addition salts have superior renin-inhibitory activities, antihypertensive activities and cholesterol-lowering activities. The .omega.-(N-acylamino)alkylphosphoryl ethanolamines are prepared by (1) reacting an .omega.-(N-acylamino) alkanol with a 2-(N-substituted amino)ethyl phosphate or its derivative, hydrolyzing the resulting product or splitting off the phosphoric acid-protective group of the resulting product thereby to form an .omega.-(N-acylamino) alkyl 2-(N-substituted amino) ethyl phosphate, and splitting off the amino-protective groups of the resulting phosphate, or (2) reacting an .omega.-(N-acylamino) alkanol with a phosphorus oxyhalide, reacting the resulting .omega.-(N-acylamino)alkyl dichlorophosphate with a 2-(N-substituted amino) ethanol, hydrolyzing the reaction product to form an .omega.-(N-acylamino) alkyl 2-(N-substituted)ethyl phosphate, and splitting off the amino-protective groups of said phosphate.

  新的.omega.-(N-酰胺基)烷基磷酰乙醇胺及其药学上可接受的酸盐加合物具有优越的肾素抑制活性、降压活性和降低胆固醇活性。该.omega.-(N-酰胺基)烷基磷酰乙醇胺的制备方法为：(1)将.omega.-(N-酰胺基)烷醇与2-(N-取代氨基)乙酸磷酸酯或其衍生物反应，水解所得产物或将所得产物的磷酸保护基裂解，从而形成.omega.-(N-酰胺基)烷基2-(N-取代氨基)乙酸磷酸酯，然后裂解所得磷酸酯的氨基保护基；或(2)将.omega.-(N-酰胺基)烷醇与磷酸氧卤反应，将所得的.omega.-(N-酰胺基)烷基二氯磷酸酯与2-(N-取代氨基)乙醇反应，水解反应产物以形成.omega.-(N-酰胺基)烷基2-(N-取代)乙酸磷酸酯，最后裂解所得磷酸酯的氨基保护基。
• Polymerization of the Inverted Hexagonal Phase
  作者：Warunee Srisiri、Thomas M. Sisson、David F. O'Brien、K. M. McGrath、Yuqi Han、Sol M. Gruner

  DOI：10.1021/ja970052x

  日期：1997.5.1

  The hydration of polar natural and synthetic lipids yields a variety of lipid phases including various inverted cubic phases and the inverted hexagonal (H-II) phase. The H-II phase can be considered as aqueous columns encased with a monolayer of lipids and arranged in a hexagonal pattern. The polar head groups are well-ordered at the water interface, whereas the lipid tails are disordered to fill the volume between the tubes of water. A particularly interesting characteristic of the H-II phase is the large temperature effect on the basis vector length d of the hexagonal lattice. Previous studies indicate that polymerization of the lipid region of the H-II phase might reduce the sensitivity of the basis vector to temperature. A phosphoethanolamine (PE) was designed and synthesized with dienoyl groups in each lipid tail in an attempt to cross-link the lipids around and along the water core of the H-II phase. The synthesis of the the PE was accomplished by acylation of 3-(4-methoxybenzyl)-sn-glycerol with 2,4,13-(E,E,Z)-docosatrienoic acid, followed by deprotection, then phosphorylation with dichloro-[[N-[(2,2,2-trichloroethoxy)carbonyl]-2-amino]ethyl]phosphinic acid to give the Troc-PE, which was converted to the PE with activated zinc and acetic acid, The hydrated PE (1/1 weight lipid/water) formed the H-II phase over an extended temperature range. Polymerization to high conversion was accomplished at 60 degrees C with the aid of redox initiators. Polymerization was followed in-situ using X-ray diffraction over a period of 48 h. The scattering, which weakened over the course of the reaction, remained consistent with a hexagonal phase. Temperature cycling of the polymerized H-II phase showed an unaltered pattern on decreasing temperature while maintaining the same lattice parameter, unlike that of the unpolymerized phase where the value increased with decreasing temperature. Thus it is possible to fix the dimensions of the H-II phase by cross-linking polymerization of appropriately designed reactive lipids.
• Lysophosphatidylethanolamine and 2-desoxylysophosphatidylethanolamine derivatives. 1. Potential renin inhibitors
  作者：Francis R. Pfeiffer、Suzanne C. Hoke、Clara K. Miao、Ralph E. Tedeschi、Josephine Pasternak、Richard Hahn、Robert W. Erickson、Herman W. Levin、Charlotte A. Burton、Jerry A. Weisbach

  DOI：10.1021/jm00288a008

  日期：1971.6
• Potential renin inhibitors. 2. Ethanolamine and ethylamine derivatives of phospholipids
  作者：Francis R. Pfeiffer、Clara K. Miao、Suzanne C. Hoke、Jerry A. Weisbach

  DOI：10.1021/jm00271a015

  日期：1972.1
• US3985875A
  申请人：——

  公开号：US3985875A

  公开（公告）日：1976-10-12